diff --git a/src/Umbraco.Web.UI.Client/src/packages/rte/tiptap/extensions/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/rte/tiptap/extensions/manifests.ts
index 8afb03e629..7e56bfe4f9 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/rte/tiptap/extensions/manifests.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/rte/tiptap/extensions/manifests.ts
@@ -22,6 +22,14 @@ const extensions: Array<ManifestTiptapExtension> = [
 		api: () => import('./tiptap-image.extension.js'),
 		meta: {},
 	},
+	{
+		type: 'tiptapExtension',
+		alias: 'Umb.Tiptap.MediaUpload',
+		name: 'Media Upload Tiptap Extension',
+		weight: 900,
+		api: () => import('./tiptap-media-upload.extension.js'),
+		meta: {},
+	},
 	{
 		type: 'tiptapExtension',
 		kind: 'button',
diff --git a/src/Umbraco.Web.UI.Client/src/packages/rte/tiptap/extensions/tiptap-media-upload.extension.ts b/src/Umbraco.Web.UI.Client/src/packages/rte/tiptap/extensions/tiptap-media-upload.extension.ts
new file mode 100644
index 0000000000..d0cf48d79e
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/rte/tiptap/extensions/tiptap-media-upload.extension.ts
@@ -0,0 +1,144 @@
+import { UmbTiptapExtensionApi } from './types.js';
+import {
+	TemporaryFileStatus,
+	UmbTemporaryFileManager,
+	type UmbTemporaryFileModel,
+} from '@umbraco-cms/backoffice/temporary-file';
+import { type Editor, UmbImage } from '@umbraco-cms/backoffice/external/tiptap';
+import { UmbId } from '@umbraco-cms/backoffice/id';
+import { UMB_NOTIFICATION_CONTEXT } from '@umbraco-cms/backoffice/notification';
+import type { UmbControllerHost } from '@umbraco-cms/backoffice/controller-api';
+
+export default class UmbTiptapMediaUploadExtension extends UmbTiptapExtensionApi {
+	/**
+	 * TODO: Implement this method when the configuration is available to extensions
+	 * @returns The maximum width of uploaded images
+	 */
+	get maxWidth() {
+		return 500;
+	}
+
+	/**
+	 * TODO: Implement this method when the configuration is available to extensions
+	 * @returns The allowed file types for uploads
+	 */
+	get allowedFileTypes() {
+		return ['image/jpeg', 'image/png', 'image/gif'];
+	}
+
+	#manager = new UmbTemporaryFileManager(this);
+	#notificationContext?: typeof UMB_NOTIFICATION_CONTEXT.TYPE;
+
+	constructor(host: UmbControllerHost) {
+		super(host);
+		this.consumeContext(UMB_NOTIFICATION_CONTEXT, (instance) => {
+			this.#notificationContext = instance;
+		});
+	}
+
+	getTiptapExtensions() {
+		// eslint-disable-next-line @typescript-eslint/no-this-alias
+		const self = this;
+		return [
+			UmbImage.extend({
+				name: 'umbMediaUpload',
+				addAttributes() {
+					return {
+						...this.parent?.(),
+						dataTmpimg: { default: null },
+					};
+				},
+				onCreate() {
+					this.parent?.();
+					const host = this.editor.view.dom;
+
+					host.addEventListener('dragover', (event) => {
+						event.preventDefault();
+						console.log('umb-media-upload.dragover', event);
+					});
+
+					host.addEventListener('drop', (event) => {
+						event.preventDefault();
+						console.log('umb-media-upload.drop', event);
+
+						const files = event.dataTransfer?.files;
+						if (!files) return;
+
+						self.#uploadTemporaryFile(files, this.editor);
+					});
+					console.log('umb-media-upload.onCreate');
+				},
+			}),
+		];
+	}
+
+	async #uploadTemporaryFile(files: FileList, editor: Editor) {
+		const filteredFiles = this.#filterFiles(files);
+		const fileModels = filteredFiles.map((file) => this.#mapFileToTemporaryFile(file));
+
+		this.dispatchEvent(new CustomEvent('rte.file.uploading', { bubbles: true, detail: fileModels }));
+
+		const uploads = await this.#manager.upload(fileModels);
+
+		uploads.forEach((upload) => {
+			if (upload.status !== TemporaryFileStatus.SUCCESS) {
+				this.#notificationContext?.peek('danger', {
+					data: {
+						headline: 'Rich Text Editor',
+						message: `Failed to upload file ${upload.file.name}`,
+					},
+				});
+				return;
+			}
+
+			editor
+				.chain()
+				.focus()
+				.setImage({
+					src: URL.createObjectURL(upload.file),
+					width: this.maxWidth.toString(),
+					dataTmpimg: upload.temporaryUnique,
+				})
+				.run();
+		});
+
+		this.dispatchEvent(new CustomEvent('rte.file.uploaded', { bubbles: true, detail: uploads }));
+	}
+
+	#mapFileToTemporaryFile(file: File): UmbTemporaryFileModel {
+		return {
+			file,
+			temporaryUnique: UmbId.new(),
+		};
+	}
+
+	#filterFiles(files: FileList): File[] {
+		return Array.from(files).filter((file) => this.allowedFileTypes.includes(file.type));
+	}
+}
+
+declare module '@tiptap/core' {
+	interface Commands<ReturnType> {
+		umbMediaUpload: {
+			/**
+			 * Add an image
+			 * @param options The image attributes
+			 * @example
+			 * editor
+			 *   .commands
+			 *   .setImage({ src: 'https://tiptap.dev/logo.png', alt: 'tiptap', title: 'tiptap logo' })
+			 */
+			setImage: (options: {
+				src: string;
+				alt?: string;
+				title?: string;
+				width?: string;
+				height?: string;
+				loading?: string;
+				srcset?: string;
+				sizes?: string;
+				dataTmpimg?: string;
+			}) => ReturnType;
+		};
+	}
+}